You've gotten a lot of good advice above.
If you are interested in going by train, here's how, from The Man In Seat 61: http://www.seat61.com/Italy.htm#London%20to%20Bologna,%20Florence,%20Rome,%20Naples
For a trip of that distance, I'd fly. Skyscanner is the way to find all your options. Be sure to select "all London airports" and "all Milan airports" to see all the options (London has 6 airports and Milan has 3, at least by the way the airlines define it). For London, Heathrow is closest; for Milan, Linate is closest. If you're using one of the others, see how much time and money is involved in getting from the city to the airport, and make sure the savings are worth the hassle. For Milan, Malpensa and Bergamo (the not-close ones) have regular bus service to the city, taking about an hour; Malpensa also has a train taking about 40 minutes. So neither of these is a real problem. I don't know the latest details about getting to and from London's airports.
If you want to fly to Rome instead, there are two airports (Fiumicino, the "main" one, and Ciampino). Either works; both have buses to the center, and Fiumicino also has a direct train.
And yes, while Ryanair has a "reputation," the other budget carriers are quite reasonable. But with any of them, be SURE you read and understand all the rules; they WILL be enforced, as that's how they make their money. For instance, if they say that any bags over 10 kilos must be checked, don't think you can get away with 10.5 kilos as carry-on; they will make you check it and charge you the higher fee for not having paid for a checked bag in advance. And as said above, do look at the "legacy" carriers like British Air and Alitalia; they may not cost more, particularly if they will check bags for free (or let you carry them on) that you would have to pay to check on a budget carrier. They will also save money if they use an airport that costs less to get to (for instance, you can get to Heathrow on the tube, but the other London airports require a train or bus).
Here's a fun musical guide to the potential perils of Cheap Flights (not safe for work-contains profanity): http://tinyurl.com/2vxmaod
As for navigating Italy, many have done it without speaking Italian. Do your research beforehand; look at guidebooks and websites so you know what to expect. Be sure to look at Rick Steves Italy, as he has lots of great tips that will make a first visit easier. And if you can learn a few basics of Italian, it will make your trip easier. You can get a single CD like Berlitz Italian (comes with handy phrasebook) as a great starter.